OSMI-1 | CAS#1681056-61-0 | OGT inhibitor

OSMI-1
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 562300

CAS#: 1681056-61-0

Description: OSMI-1 is an inhibitor of O-GlcNAc transferase (OGT).

Chemical Structure

OSMI-1

CAS# 1681056-61-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562300
Name: OSMI-1
CAS#: 1681056-61-0
Chemical Formula: C28H25N3O6S2
Exact Mass: 563.12
Molecular Weight: 563.643
Elemental Analysis: C, 59.67; H, 4.47; N, 7.46; O, 17.03; S, 11.38

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 260
10mg	USD 450
25mg	USD 890
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: OSMI-1; OSMI 1; OSMI1;

IUPAC/Chemical Name: (R)-N-(Furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide

InChi Key: IYIGLWQQAMROOF-HHHXNRCGSA-N

InChi Code: InChI=1S/C28H25N3O6S2/c1-36-25-9-3-2-8-23(25)27(28(33)31(17-20-6-4-14-37-20)18-21-7-5-15-38-21)30-39(34,35)22-11-12-24-19(16-22)10-13-26(32)29-24/h2-16,27,30H,17-18H2,1H3,(H,29,32)/t27-/m1/s1

SMILES Code: O=C(N(CC1=CC=CO1)CC2=CC=CS2)[C@@H](C3=CC=CC=C3OC)NS(=O)(C4=CC5=C(NC(C=C5)=O)C=C4)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	OSMI-1 is an inhibitor of O-GlcNAc transferase (OGT).
In vitro activity:	This study reports a small molecule OGT inhibitor, OSMI-1, developed from a high-throughput screening hit. It is cell-permeable and inhibits protein O-GlcNAcylation in several mammalian cell lines without qualitatively altering cell surface N- or O-linked glycans. The development of this molecule validates high-throughput screening approaches for the discovery of glycosyltransferase inhibitors, and further optimization of this scaffold may lead to yet more potent OGT inhibitors useful for studying OGT in animal models. Reference: ACS Chem Biol. 2015 Jun 19;10(6):1392-7. https://pubmed.ncbi.nlm.nih.gov/25751766/
In vivo activity:	This study demonstrated that the combination of DOX and OSMI-1 stimulated cell death, dramatically reducing cell proliferation and tumor growth in vivo using a HepG2 xenograft mouse model. These findings indicate that OSMI-1 acts as a potential chemosensitizer by enhancing DOX-induced cell death. Reference: Cancers (Basel). 2020 Oct 27;12(11):3154. https://pubmed.ncbi.nlm.nih.gov/33121131/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	25.0	44.35
	DMF:PBS (pH 7.2) (1:5)	0.2	0.28
	DMSO	73.3	130.11

Preparing Stock Solutions

The following data is based on the product molecular weight 563.64 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Papanicolaou KN, Jung J, Ashok D, Zhang W, Modaressanavi A, Avila E, Foster DB, Zachara NE, O'Rourke B. Inhibiting O-GlcNAcylation impacts p38 and Erk1/2 signaling and perturbs cardiomyocyte hypertrophy. J Biol Chem. 2023 Mar;299(3):102907. doi: 10.1016/j.jbc.2023.102907. Epub 2023 Jan 13. PMID: 36642184; PMCID: PMC9988579. 2.Ortiz-Meoz RF, Jiang J, Lazarus MB, Orman M, Janetzko J, Fan C, Duveau DY, Tan ZW, Thomas CJ, Walker S. A small molecule that inhibits OGT activity in cells. ACS Chem Biol. 2015 Jun 19;10(6):1392-7. doi: 10.1021/acschembio.5b00004. Epub 2015 Mar 18. PMID: 25751766; PMCID: PMC4475500. 3. Lee SJ, Kwon OS. O-GlcNAc Transferase Inhibitor Synergistically Enhances Doxorubicin-Induced Apoptosis in HepG2 Cells. Cancers (Basel). 2020 Oct 27;12(11):3154. doi: 10.3390/cancers12113154. PMID: 33121131; PMCID: PMC7693581.
In vitro protocol:	1. Papanicolaou KN, Jung J, Ashok D, Zhang W, Modaressanavi A, Avila E, Foster DB, Zachara NE, O'Rourke B. Inhibiting O-GlcNAcylation impacts p38 and Erk1/2 signaling and perturbs cardiomyocyte hypertrophy. J Biol Chem. 2023 Mar;299(3):102907. doi: 10.1016/j.jbc.2023.102907. Epub 2023 Jan 13. PMID: 36642184; PMCID: PMC9988579. 2.Ortiz-Meoz RF, Jiang J, Lazarus MB, Orman M, Janetzko J, Fan C, Duveau DY, Tan ZW, Thomas CJ, Walker S. A small molecule that inhibits OGT activity in cells. ACS Chem Biol. 2015 Jun 19;10(6):1392-7. doi: 10.1021/acschembio.5b00004. Epub 2015 Mar 18. PMID: 25751766; PMCID: PMC4475500.
In vivo protocol:	1. Lee SJ, Kwon OS. O-GlcNAc Transferase Inhibitor Synergistically Enhances Doxorubicin-Induced Apoptosis in HepG2 Cells. Cancers (Basel). 2020 Oct 27;12(11):3154. doi: 10.3390/cancers12113154. PMID: 33121131; PMCID: PMC7693581.

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1: Park SK, Zhou X, Pendleton KE, Hunter OV, Kohler JJ, O'Donnell KA, Conrad NK. A Conserved Splicing Silencer Dynamically Regulates O-GlcNAc Transferase Intron Retention and O-GlcNAc Homeostasis. Cell Rep. 2017 Aug 1;20(5):1088-1099. doi: 10.1016/j.celrep.2017.07.017. PubMed PMID: 28768194; PubMed Central PMCID: PMC5588854.

2: Angelova M, Ortiz-Meoz RF, Walker S, Knipe DM. Inhibition of O-Linked N-Acetylglucosamine Transferase Reduces Replication of Herpes Simplex Virus and Human Cytomegalovirus. J Virol. 2015 Aug;89(16):8474-83. doi: 10.1128/JVI.01002-15. Epub 2015 Jun 3. PubMed PMID: 26041297; PubMed Central PMCID: PMC4524265.

3: Ortiz-Meoz RF, Jiang J, Lazarus MB, Orman M, Janetzko J, Fan C, Duveau DY, Tan ZW, Thomas CJ, Walker S. A small molecule that inhibits OGT activity in cells. ACS Chem Biol. 2015 Jun 19;10(6):1392-7. doi: 10.1021/acschembio.5b00004. Epub 2015 Mar 18. PubMed PMID: 25751766; PubMed Central PMCID: PMC4475500.

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